Diisopropylethylamine → 5-Allylpyrazin-2-amine
反応式
[NH2:1][C:2]1[CH:7]=[N:6][C:5](Br)=[CH:4][N:3]=1.[CH2:9]([Sn](CCCC)(CCCC)CCCC)[CH:10]=[CH2:11].[Cl-].[Li+].C(N(CC)C(C)C)(C)C.[F-].[K+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:11]([C:5]1[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1)[CH:10]=[CH2:9]参加物
反応条件
- 温度
- 120 °C
実験手順
A mixture of 2-amino-5-bromopyrazine (1.00 g, 5.746 mmol), tetrakis(triphenylphosphine)palladium(0) (132 mg, 0.114 mmol), allyltri-n-butyltin (2.2 mL, 7.096 mmol), lithium chloride (875.0 mg, 20.64 mmol) and N,N-diisopropylethylamine (2.6 mL, 14.93 mmol) in N,N-dimethylformamide (29 mL) was stirred at 120° C. for 45 min. The reaction mixture was cooled to 25° C. and then treated with a saturated aqueous potassium fluoride solution (20 mL). The mixture was stirred for 3 h, treated with a solution of water and a saturated aqueous sodium chloride solution, and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 1/1 hexanes/ethyl acetate) afforded 5-allyl-pyrazin-2-ylamine (378.2 mg, 48.7%) as a yellow solid: LRMS for C7H9N3 (M+H)+ at m/z=136.
後処理
- temperatureThe reaction mixture was cooled to 25° C.
- stirringThe mixture was stirred for 3 h
- extractiona saturated aqueous sodium chloride solution, and extracted with ethyl acetate
- dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
出典と根拠
- ORDレコード
- ord-22fdde7b365142a5a1c65e27638e55fd
- 出典データセット
- uspto-grants-2006_11
- 特許番号
- US07132425B2
反応ノート
読み込み中…